2-Alkylamino-6-[1-(2,6-difluorophenyl)alkyl]-3,4-dihydro-5-alkylpyrimidin-4(3H)-ones (F2-NH-DABOs) 4, 5 belonging to the dihydro-alkoxy-benzyl-oxopyrimidine (DABO) family and bearing different alkyl- and arylamino side chains at the C2-position of the pyrimidine ring were designed as active agai...

Addition of 2-(chloromagnesiomethyl)-2-propenyl ethers 1a and 1b to epoxides 3 affords ring opening products 6 or 7 which are converted by Pd(0) to 3-methylenetetrahydropyrans 9. Cyclization of the addition products is best effected by a catalyst system generated in situ from Pd(OAc)2 and (i-PrO)3P.

The meta-photoadditions of cis-cyclooctene to anisole and toluene are shown to proceed via 2,6-bonding to the aromatic rings, in contrast to previous reports.

Site selectivity, regioselectivity and stereoselectivity of [2+3] cycloaddition of 4-trifluoromethylbenzonitrile oxide to cyclohexene carboxylates substituted with alkenyl functions were examined. Site selectivity was correlated with electron charges of alkenyl carbon atoms. Structure of the pro...

The addition of N-methoxymethyl-N-organylcarbamoyl(trimethyl)silane to α-ketoesters in anhydrous toluene at 60 °C afforded α-alkoxycarbonyl-α-siloxy amides in high yields (75–96%). The methoxymethyl was used as an amino protecting group and could be easily converted into hydrogen atom by si...

4,5-Disubstituted and 4-substituted alkyl 2-amino-thiophene-3-carboxylates react with triethyl orthoformate and sodium azide in acetic acid to yield new 2-(1H-tetrazol-1-yl)-4-R1-5-R2-thiophene derivates. It was established that the reaction of these tetrazoles with hydrazine generates the insuf...

The synthesis of 2,3,4-substituted pyridine derivatives useful as scaffolds in the development of peptidomimetics is described. The use of a variety of electrophiles in a halogen-dance reaction to produce 3-alkyl-2-fluoro-4-iodo-pyridine derivatives as ‘functionalized scaffolds’ and the possib...

A one-pot, synthesis of N-arylsulfonyl-2-iminocoumarins is developed at ambient temperature by the reaction of 2-hydroxybenzaldehydes, arylacetonitriles, and aryl sulfonyl chlorides using DABCO as a base in a bio-mass-derived green solvent 2-MethylTHF. A simple telescoped process in which 2H-chr...

An unprecedented and convenient synthetic approach to 2,3-dihydro-1H-isoindol-1-one (isoindolinone) derivatives has been developed. The key and final step of the method is the reaction of N-alkyl-N-(o-bromobenzyl)benzamides with butyllithium in THF at −78 °C. The corresponding 2-alkyl-3-aryl-2,...

A Cu(OAc)2-catalyzed synthesis of 2-arylquinoline N-oxides with easily available arylamines is described. The main features of this reaction are mild reaction conditions, high functional-group tolerance, excellent regioselectivity, and good to excellent yields. This procedure is mild, operationa...

A series Rh(III)-catalyzed ortho-selective C–H halogenation of 2-arylbenzo[d]thiazoles has been developed using N-halosuccinimides (NXS, X=Br and I) as halogen sources. ortho-Brominated and iodinated various 2-arylbenzo[d]thiazoles could be accessed in good to excellent yields and high regiosel...

An intermolecular Ugi reaction of 2-(1-(aminomethyl)cyclohexyl)acetic acid (gabapentin) with glyoxal and cyclohexyl isocyanide or aromatic aldehyde and tertbutyl isocyanide under mild conditions in ethanol have been developed to produce two novel class of N-cyclohexyl-3-(aryl)-3-oxo-2-(3-oxo-2-a...

The Cu2O-catalyzed reaction between equimolar amounts of easily available 3-substituted-2-bromo-2-propen-1-ols and dicyclohexyl carbodiimide in DMSO at 100 °C using K3PO4 as the base and in the absence of any additive exclusively delivers substituted 2-iminooxazolidines with yields up to 80%. T...

Densities of dilute aqueous solutions of three branched diols derived from propane-1,3-diol (2-methyl-2-propylpropane-1,3-diol, 2,2-diethylpropane-1,3-diol, and 2-ethyl-2-butylpropane-1,3-diol) and of 3-methylpentane-1,5-diol measured over the temperature range from (298 to 573) K and at pressur...

A versatile new approach for the synthesis in three steps of 2-substituted-2,3-dihydro[1,4]dioxino[2,3-b]pyridines B via a Smiles rearrangement using easily available reagents is described. A study illustrating the influence of experimental conditions on the progress of the reaction is reported.

We report the discovery of a novel benzylpiperidine derivative with serotonin transporter (SERT) inhibitory activity and 5-HT1A receptor weak partial agonistic activity showing the antidepressant-like effect. The 3-methoxyphenyl group and the phenethyl group of compound 1, which has weak SERT bi...

The mass spectrometric fragmentation of 1-(N-ethoxycarbonylamino)arylmethylphosphonic monoesters has been investigated under positive ion electrospray ionization conditions. All protonated title compounds predominantly eliminate a phosphite monoester via a four-membered ring hydrogen rearrangeme...

We describe two new closely related total syntheses of naphtho[2,1-f]isoquinolines. The first synthesis consists of a Heck coupling reaction between trifluoromethanesulfonic acid 2-(2-ethoxycarbonylaminoethyl)phenyl esters and styrenes to give [2-(2-styrylphenyl)ethyl]carbamic acid ethyl esters....

Using the molecular recognizability of guanidinium o-terphenyl-4,4′-disulfonate (G2o-TPDS) host compound to guests, the stereoisomers of dimethylcyclohexane (DMCH) were separated. In a binary competition of cis- and trans-isomers of 1,2-, 1,3- and 1,4-DMCH, it was found that the equatorial, equ...

Monodisperse MIL-125(Ti) Metal-Organic Framework crystals were synthesized and studied as stationary phase in high performance liquid chromatography (HPLC). Different pure compounds and model mixtures (including stereoisomer mixtures) were injected from which chromatographic parameters, includin...